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| 1st(1st leg) | Torino FC | - | AC Milan | 2:0 (2:0) | ||
| 2nd (2nd leg) | AC Milan | - | Torino FC | 3:0 (0:0) | ||
| 1st(1st leg): 08/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: AC Milan | ||||
| 1st(1st leg) | Cagliari Calcio | - | AC Venezia | 0:0 (0:0) | ||
| 2nd (2nd leg) | AC Venezia | - | Cagliari Calcio | 2:1 (1:1) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: AC Venezia | ||||
| 1st(1st leg) | Reggina Calcio | - | Bologna FC | 1:1 (0:1) | ||
| 2nd (2nd leg) | Bologna FC | - | Reggina Calcio | 3:0 (2:0) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: Bologna FC | ||||
| 1st(1st leg) | Sampdoria | - | Hellas Verona | 2:0 (1:0) | ||
| 2nd (2nd leg) | Hellas Verona | - | Sampdoria | 1:0 (1:0) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: Sampdoria | ||||
| 1st(1st leg) | US Lecce | - | Piacenza Calcio | 1:2 (0:0) | ||
| 2nd (2nd leg) | Piacenza Calcio | - | US Lecce | 2:3 (1:1, 1:2) aet | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: US Lecce | ||||
| 1st(1st leg) | Calcio Padova | - | ACF Fiorentina | 0:1 (0:0) | ||
| 2nd (2nd leg) | ACF Fiorentina | - | Calcio Padova | 2:0 (0:0) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: ACF Fiorentina | ||||
| 1st(1st leg) | Atalanta | - | Empoli FC | 2:1 (0:1) | ||
| 2nd (2nd leg) | Empoli FC | - | Atalanta | 0:0 (0:0) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: Atalanta | ||||
| 1st(1st leg) | Chievo Verona | - | AS Roma | 2:2 (2:0) | ||
| 2nd (2nd leg) | AS Roma | - | Chievo Verona | 2:1 (0:1) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 22/09/1998 | Winner: AS Roma | ||||
| 1st(1st leg) | SS Gualdo | - | Udinese Calcio | 2:2 (0:1) | ||
| 2nd (2nd leg) | Udinese Calcio | - | SS Gualdo | 4:0 (3:0) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: Udinese Calcio | ||||
| 1st(1st leg) | Brescia Calcio | - | Vicenza Calcio | 3:2 (1:0) | ||
| 2nd (2nd leg) | Vicenza Calcio | - | Brescia Calcio | 3:0 (1:0) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: Vicenza Calcio | ||||
| 1st(1st leg) | Parma AC | - | Genoa CFC | 3:0 (1:0) | ||
| 2nd (2nd leg) | Genoa CFC | - | Parma AC | 0:1 (0:0) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: Parma AC | ||||
| 1st(1st leg) | Lucchese | - | AS Bari | 1:0 (0:0) | ||
| 2nd (2nd leg) | AS Bari | - | Lucchese | 2:0 (0:0) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: AS Bari | ||||
| 1st(1st leg) | Lazio Roma | - | Cosenza Calcio | 2:1 (0:0) | ||
| 2nd (2nd leg) | Cosenza Calcio | - | Lazio Roma | 0:2 (0:1) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: Lazio Roma | ||||
| 1st(1st leg) | Castel di Sangro | - | Salernitana Sport | 0:0 (0:0) | ||
| 2nd (2nd leg) | Salernitana Sport | - | Castel di Sangro | 0:2 (0:1) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: Castel di Sangro | ||||
| 1st(1st leg) | Inter | - | AC Cesena | 1:0 (1:0) | ||
| 2nd (2nd leg) | AC Cesena | - | Inter | 0:0 (0:0) | ||
| 1st(1st leg): 09/09/1998 | 2nd (2nd leg): 24/09/1998 | Winner: Inter | ||||
| 1st(1st leg) | Ravenna Calcio | - | Juventus | 0:2 (0:0) | ||
| 2nd (2nd leg) | Juventus | - | Ravenna Calcio | 4:0 (1:0) | ||
| 1st(1st leg): 10/09/1998 | 2nd (2nd leg): 23/09/1998 | Winner: Juventus | ||||
